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1.
Phytomedicine ; 101: 154108, 2022 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-35472694

RESUMO

BACKGROUND: Canthin-6-one (CO) is an active ingredient found in Picrasma quassioides (D.Don) Benn. (PQ) that displays various biological activities including anti-inflammatory properties. Several studies reported PQ displayed neuroprotective activities, but its effects on astrocytes have not yet been investigated. Astrocytes are crucial regulators of neuroinflammatory responses under pathological conditions in the central nervous system (CNS). Proinflammatory astrocytes can induce the blood-brain barrier (BBB) breakdown, which plays a key role in the progression of neurodegenerative disorder (ND). PURPOSE: This study aims to investigate the anti-neuroinflammatory effects of CO in LPS-induced astrocyte activation and its underlying mechanisms in protecting the blood-brain barrier (BBB) in vitro. METHODS: Mouse astrocytes (C8-D1A) were activated with lipopolysaccharide (LPS) with or without CO pretreatment. Effects of CO on astrocyte cell viability, secretions of tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), interleukin-1ß (IL-1ß) and nitric oxide (NO) were determined. Intracellular transcriptions and translations of proinflammatory mediators, molecular signaling, [Ca2+] and the levels of reactive oxygen species (ROS) were evaluated by RT-PCR, western blotting, and flow cytometry, respectively. Astrocyte-conditioned medium (ACM) was further prepared for incubating endothelial monolayer (bEnd.3) grown on transwell. Endothelial disruptions were evaluated by transendothelial electrical resistance (TEER), FITC-dextran permeability and monocyte adhesion assays. Endothelial tight junctions (TJs) and molecular signaling pathways were evaluated by immunofluorescence staining and western blotting. RESULTS: CO attenuated LPS-induced expression of astrocytic proinflammatory mediators (TNF-α, IL-1ß, IL-6, NO) and inhibited deleterious molecular activities including inducible nitric oxide synthase (iNOS), p-NFκB and p-STAT3 in astrocytes. Incubation of ACM collected from CO-treated astrocytes significantly ameliorated endothelial disruptions, reduced expressions of endothelial cytokine receptors (IL-6R, gp130 (IL-6RB), TNFR and IL-1R), suppressed proinflammatory pathways, MAPKs (p-AKT, p-MEK, p-ERK, p-p38, p-JNK) and p-STAT3, restored endothelial stabilizing pathways (p-Rac 1) and upregulated beneficial endothelial nitric oxide synthase (eNOS). CONCLUSION: Our study demonstrates for the first time CO exhibited potent protective effects against astrocyte-mediated proinflammatory responses and associated endothelial barrier disruptions.


Assuntos
Lipopolissacarídeos , Picrasma , Animais , Astrócitos , Encéfalo/metabolismo , Carbolinas , Alcaloides Indólicos , Interleucina-6/metabolismo , Lipopolissacarídeos/farmacologia , Camundongos , Óxido Nítrico Sintase Tipo II/metabolismo , Picrasma/metabolismo , Fator de Necrose Tumoral alfa/metabolismo
2.
Phytochemistry ; 193: 112987, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34768188

RESUMO

Picrasma quassioides, a member of the Simaroubaceae family, is the subject of research in numerous pharmacological and chemical studies. This plant mainly contains alkaloids, quassinoids and terpenoids. These molecules exhibit various pharmacological benefits, such as anti-inflammatory, anticancer, and anti-viral effects, on the cardiovascular system. Alkaloids make up the majority of these molecules. This review describes 127 alkaloid substances from P. quassioides. These alkaloids can be divided into the following classes: ß-carbolines, canthinones and alkaloid dimers. A compilation of their nuclear magnetic resonance spectroscopy data and possible biosynthetic pathways of these compounds and the pharmacological effects of P. quassioides are also included.


Assuntos
Alcaloides , Picrasma , Alcaloides/farmacologia , Vias Biossintéticas , Espectroscopia de Ressonância Magnética , Estrutura Molecular
3.
J Ethnopharmacol ; 280: 114441, 2021 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-34302942

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: The genus Picrasma belongs to the Simaroubaceae family and contains six species which are mainly distributed in tropical and subtropical regions of Asia and America. The barks, roots, stems, branches, or leaves of several Picrasma species have been applied as folk medicines to treat fever, sore throat, dysentery, eczema, nausea, loss of appetite, diabetes mellitus, cancer, and hypertension. AIM OF THE STUDY: A systematic summary on the botanic characterization, ethnopharmacological uses, phytochemistry, bioactivities and toxicity of species belonging to Picrasma was presented to facilitate the exploitation of the therapeutic potential of these plants. MATERIALS AND METHODS: The literatures about Picrasma were retrieved from a series of scientific search engines including Web of Science, SciFinder, PubMed, CNKI, Google Scholar, Elsevier, Wiley, ACS publications, and SpringerLink between 1970 and 2020. Plant names were validated by "The Plant List" (www.theplantlist.org). RESULTS: As ethnopharmacological uses, Picrasma species are valuable folk medicines to treat fever, inflammation, dysentery, eczema, cancer, diabetics, skin infection, and so on. Up to now, a total of 361 compounds including 126 alkaloids, 132 quassinoids, 67 triterpenoids, and 36 miscellaneous compounds were reported from Picrasma species. Quassinoids and alkaloids are the principal constituents in the genus. The extracts and phytochemical constituents of Picrasma species demonstrate a wide range of bioactivities including cytotoxic, anti-inflammatory, antimicrobial, and other activities. CONCLUSIONS: Picrasma species are widely used as traditional medicines, have diverse chemical constituents with obvious biological activities. Nevertheless, further studies are required on the Picrasma species to assert the ethnopharmacological uses, clarify their bioactive constituents, determine pharmacological actions, and toxicity. Therefore, the present review may provide a critical clue for future studies and further exploitations on Picrasma species.


Assuntos
Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/toxicidade , Fitoterapia , Picrasma , Plantas Medicinais/química , Etnofarmacologia , Humanos , Compostos Fitoquímicos/química
4.
J Nat Prod ; 84(8): 2111-2120, 2021 08 27.
Artigo em Inglês | MEDLINE | ID: mdl-34197108

RESUMO

A bioactivity-guided study on the leaves of Picrasma javanica led to the isolation of 19 quassinoids, including 13 new compounds. The structures of the new compounds were elucidated by a combination of spectroscopic data analysis, X-ray crystallography studies, and electronic circular dichroism (ECD) data interpretation. Compounds 1-7 are rare examples of quassinoids with a keto carbonyl group at C-12. The biological activities of 11 of the more abundant isolates were evaluated against five phytopathogenic fungi in vitro, and several of them including 6 and 15 showed moderate inhibitory effects that were comparative to those of the positive control, carbendazim. In addition, the preliminary structure-activity relationships (SARs) of these quassinoids were also investigated.


Assuntos
Fungos/efeitos dos fármacos , Fungicidas Industriais/farmacologia , Picrasma/química , Quassinas/farmacologia , China , Fungos/patogenicidade , Fungicidas Industriais/química , Estrutura Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Picrasma/microbiologia , Extratos Vegetais/química , Folhas de Planta/química , Quassinas/química , Relação Estrutura-Atividade
5.
Oncol Rep ; 46(2)2021 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-34165177

RESUMO

Nasopharyngeal carcinoma (NPC) is an indicator disease in Asia due to its unique geographical and ethnic distribution. Dehydrocrenatidine (DC) is a ß­carboline alkaloid abundantly present in Picrasma quassioides (D. Don) Benn, a deciduous shrub or small tree native to temperate regions of southern Asia, and ß­carboline alkaloids play anti­inflammatory and antiproliferative roles in various cancers. However, the mechanism and function of DC in human NPC cells remain only partially explored. The present study aimed to examine the cytotoxicity and biochemical role of DC in human NPC cells. The MTT method, cell cycle analysis, DAPI determination, Annexin V/PI double staining, and mitochondrial membrane potential examination were performed to evaluate the effects of DC treatment on human NPC cell lines. In addition, western blotting analysis was used to explore the effect of DC on apoptosis and signaling pathways in related proteins. The analysis results confirmed that DC significantly reduced the viability of NPC cell lines in a dose­ and time­dependent manner and induced apoptosis through internal and external apoptotic pathways (including cell cycle arrest, altered mitochondrial membrane potential, and activated death receptors). Western blot analysis illustrated that DC's effect on related proteins in the mitogen­activated protein kinase pathway can induce apoptosis by enhancing ERK phosphorylation and inhibiting Janus kinase (JNK) phosphorylation. Notably, DC induced apoptosis by affecting the phosphorylation of JNK and ERK, and DC and inhibitors (SP600125 and U0126) in combination restored the overexpression of p­JNK and p­ERK. To date, this is the first study to confirm the apoptosis pathway induced by DC phosphorylation of p­JNK and p­REK in human NPC. On the basis of evidence obtained from this study, DC targeting the inhibition of NPC cell lines may be a promising future strategy for NPC treatment.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Carbolinas/farmacologia , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Carcinoma Nasofaríngeo/metabolismo , Neoplasias Nasofaríngeas/metabolismo , Picrasma/química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Humanos , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Carcinoma Nasofaríngeo/tratamento farmacológico , Neoplasias Nasofaríngeas/tratamento farmacológico , Fosforilação/efeitos dos fármacos , Extratos Vegetais/química
6.
Phytochemistry ; 184: 112675, 2021 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-33548770

RESUMO

Seven undescribed tirucallane-type triterpenoids, kumunorquassins A‒E and kumuquassins K and L, along with nine known analogues, have been isolated from the leaves of Picrasma quassioides (D. Don) Benn. Their structures and absolute configurations were elucidated based on comprehensive spectroscopic analyses, single-crystal X-ray diffraction analysis and electronic circular dichroism (ECD). The absolute configuration of cornusalterin J was unequivocally determined by X-ray diffraction based on its p-bromobenzoate derivative. A brief approach was presented in our study, which could rapidly and conveniently determine the relative and absolute configurations of OCH3-23 of kumuquassin L and cornusalterins J, H and G depending on the chemical shift differences (Δδ) of C-24 and C-25 and the chemical shifts of C-23, H-23 and H-24. In addition, the cytotoxicities of these compounds against two human tumour cell lines (HepG2 and Hep3B) were evaluated.


Assuntos
Picrasma , Triterpenos , Estrutura Molecular , Folhas de Planta , Triterpenos/farmacologia
7.
J Asian Nat Prod Res ; 23(3): 217-227, 2021 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-32102545

RESUMO

Four new alkaloids (1-4) and one known alkaloid were isolated from the stems of Picrasma quassioides. The structures of these isolated compounds were elucidated by spectroscopic analyses, a combination of computer-assisted structure elucidation software (ACD/Structure Elucidator) and gauge-including atomic orbital (GIAO) calculation of 1 D NMR data. All compounds were evaluated for their cytotoxic activities against hepatocellular carcinoma HepG2 and Hep3B cells. However, they did not show obvious inhibitory activities.[Figure: see text].


Assuntos
Alcaloides , Neoplasias Hepáticas , Picrasma , Alcaloides/farmacologia , Computadores , Humanos , Estrutura Molecular
8.
Nat Prod Res ; 35(21): 3687-3693, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-32056448

RESUMO

Three new phenolic derivatives, picraquanines A-C (1-3), along with 6 known ones 4-9 were obtained from the stems of Picrasma quassioides (D. Don) Benn. The new structures were determined by extensive spectroscopic data analysis, including IR, HRESIMS, 1H-NMR, 13C-NMR, HSQC, HMBC, 1H-1H COSY experiments. The absolute configuration of 1 was determined by comparison of its experimental and calculated ECD spectra. Furthermore, all the compounds were tested for their nitric oxide (NO) inhibitory effects against LPS-stimulated RAW 264.7 cells, however, none of them exhibited inhibitory effects (IC50 >100 µM).[Figure: see text].


Assuntos
Picrasma , Animais , Camundongos , Estrutura Molecular , Óxido Nítrico , Fenóis , Células RAW 264.7
9.
Nutrients ; 12(9)2020 Aug 26.
Artigo em Inglês | MEDLINE | ID: mdl-32858812

RESUMO

Picrasma quassioides is a member of the Simaroubaceae family commonly grown in the regions of Asia, the Himalayas, and India and has been used as a traditional herbal medicine to treat various illnesses such as fever, gastric discomfort, and pediculosis. This study aims to critically review the presence of phytochemicals in P. quassioides and correlate their pharmacological activities with the significance of its use as traditional medicine. Data were collected by reviewing numerous scientific articles from several journal databases on the pharmacological activities of P. quassioides using certain keywords. As a result, approximately 94 phytochemicals extracted from P. quassioides were found to be associated with quassinoids, ß-carbolines and canthinones. These molecules exhibited various pharmacological benefits such as anti-inflammatory, antioxidant, anti-cancer, anti-microbial, and anti-parasitic activities which help to treat different diseases. However, P. quassioides were also found to have several toxicity effects in high doses, although the evidence regarding these effects is limited in proving its safe use and efficacy as herbal medicine. Accordingly, while it can be concluded that P. quassioides may have many potential pharmacological benefits with more phytochemistry discoveries, further research is required to determine its real value in terms of quality, safety, and efficacy of use.


Assuntos
Medicina Tradicional/métodos , Compostos Fitoquímicos/farmacologia , Picrasma , Extratos Vegetais/farmacologia , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/uso terapêutico , Antimaláricos/farmacologia , Antimaláricos/uso terapêutico , Antineoplásicos/farmacologia , Antineoplásicos/uso terapêutico , Antioxidantes/farmacologia , Antioxidantes/uso terapêutico , Humanos , Compostos Fitoquímicos/uso terapêutico , Extratos Vegetais/uso terapêutico , Úlcera/prevenção & controle
10.
Bioorg Chem ; 101: 104043, 2020 08.
Artigo em Inglês | MEDLINE | ID: mdl-32629286

RESUMO

Nine new N-methoxy-ß-carboline alkaloids (NMCAs) (1a/1b-3a/3b and 4-6) and two known NMCAs (7 and 8) were isolated from the stems of Picrasma quassioides. Their structures were elucidated by spectroscopic data analyses, quantum chemical calculations, and single-crystal X-ray crystallographic data. An analysis of the 13C NMR chemical shifts of the N-methoxy groups in these NMCAs and 41 gathered known compounds reveals the phenomenon that the chemical shifts of all these N-methoxy groups are greater than δC 62, which can be used to recognize the N-methoxy group rapidly. In addition, the acetylcholinesterase (AChE) and Aß42 aggregation inhibitory activities of 1-8 were evaluated. Compounds 1, 2, 7, and 8 displayed AChE inhibitory activity with IC50 values of 14.9, 13.2, 17.6, and 43.9 µM, respectively. Compound 2 showed inhibition activity against Aß42 aggregation with an IC50 value of 10.1 µM.


Assuntos
Alcaloides/química , Peptídeos beta-Amiloides/efeitos dos fármacos , Fragmentos de Peptídeos/efeitos dos fármacos , Picrasma/química , Acetilcolinesterase , Humanos , Estrutura Molecular , Relação Estrutura-Atividade
11.
Anticancer Res ; 40(7): 3819-3830, 2020 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-32620621

RESUMO

BACKGROUND: Picrasma quassioides (PQ) is a traditional Asian herbal medicine with anti-tumor properties that can inhibit the viability of HepG2 liver cancer cells. H-Ras is often mutated in liver cancer, however, the effect of PQ treatment on H-Ras mutated liver cancer is unclear. This study aimed to investigate the role of PQ on ROS accumulation and mitochondrial dysfunction in H-ras mutated HepG2 (HepG2G12V) cells. MATERIALS AND METHODS: PQ ethanol extract-induced HepG2G12V apoptosis was analyzed by the MTT assay, fluorescence microscopy, flow cytometry and western blotting. RESULTS: PQ treatment affected cell migration and colony formation in HepG2G12V cells. Cleaved-caspase-3, cleaved-caspase-9 and BCL2 associated agonist of cell death (BAD) expression levels were increased, while the levels of B-cell lymphoma-extra large (Bcl-xL) were decreased with PQ treatment. PQ treatment led to a reduction of H-Ras expression levels in liver cancer cells, thus reducing their abnormal proliferation. Furthermore, it led to increased expression levels of Peroxiredoxin VI, which regulates the redox signal in cells. CONCLUSION: Taken together these results provide a new functional significance for the role of PQ in treating HepG2G12V liver cancer.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Neoplasias Hepáticas/tratamento farmacológico , Mitocôndrias Hepáticas/efeitos dos fármacos , Extratos Vegetais/farmacologia , Proteínas Proto-Oncogênicas p21(ras)/genética , Espécies Reativas de Oxigênio/metabolismo , Apoptose/efeitos dos fármacos , Movimento Celular/efeitos dos fármacos , Genes ras , Células Hep G2 , Humanos , Neoplasias Hepáticas/genética , Neoplasias Hepáticas/metabolismo , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Mitocôndrias Hepáticas/metabolismo , Picrasma/química , Proteínas Proto-Oncogênicas p21(ras)/biossíntese
12.
In Vivo ; 34(4): 1823-1833, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32606152

RESUMO

BACKGROUND/AIM: Picrasma quassioides (P. quassioides) is used in traditional Asian medicine widely for the treatment of anemopyretic cold, eczema, nausea, loss of appetite, diabetes mellitus, hypertension etc. In this study we aimed to understand the effect of P. quassioides ethanol extract on SiHa cervical cancer cell apoptosis. MATERIALS AND METHODS: The P. quassioides extract-induced apoptosis was analyzed using the MTT assay, fluorescence microscopy, flow cytometry and western blotting. RESULTS: P. quassioides extract induced cellular apoptosis by increasing the accumulation of cellular and mitochondrial reactive oxygen species (ROS) levels and inhibiting ATP synthesis. Pretreatment with N-Acetylcysteine (NAC), a classic antioxidant, decreased the intracellular ROS production and inhibited apoptosis. In addition, the P38 MAPK signaling pathway is a key in the apoptosis of SiHa cells induced by the P. quassioides extract. CONCLUSION: The P. quassioides extract exerts its anti-cancer properties on SiHa cells through ROS-mitochondria axis and P38 MAPK signaling. Our data provide a new insight for P. quassioides as a therapeutic strategy for cervical cancer treatment.


Assuntos
Picrasma , Neoplasias do Colo do Útero , Apoptose , Feminino , Humanos , Potencial da Membrana Mitocondrial , Mitocôndrias/metabolismo , Picrasma/metabolismo , Espécies Reativas de Oxigênio , Transdução de Sinais , Neoplasias do Colo do Útero/tratamento farmacológico , Neoplasias do Colo do Útero/genética , Proteínas Quinases p38 Ativadas por Mitógeno/genética
13.
J Nat Med ; 74(3): 571-578, 2020 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-32328863

RESUMO

Three new quassinoids, javanicinols A and B (1 and 2) and 4-keto-(16S)-methoxyjavanicin B (3), together with three known quassinoids (4-6) were isolated from the chloroform-soluble fraction of the methanol extract of the Picrasma javanica wood. The structures of 1-3 were determined by spectroscopic analyses, including 1D and 2D NMR, HRESIMS, and CD. The anti-HIV-1 viral protein R (Vpr) assay revealed that 1 and 2 exhibited potent anti-Vpr activities at 1.25 µM. Furthermore, the assay also revealed the potent anti-Vpr activities of (16R)-methoxyjavanicin B (7) and (16S)-methoxyjavanicin B (8), which were previously isolated from the Picrasma javanica wood.


Assuntos
Fármacos Anti-HIV/farmacologia , Produtos do Gene vpr/antagonistas & inibidores , HIV-1/efeitos dos fármacos , Picrasma/química , Quassinas/farmacologia , Fármacos Anti-HIV/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Quassinas/química , Quassinas/isolamento & purificação , Madeira/química
14.
Biomed Chromatogr ; 34(7): e4830, 2020 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-32175611

RESUMO

5-methoxycanthin-6-one, a major canthinone alkaloid isolated from Picrasma quassioides, exhibited significant pharmacological activities. In this study, a rapid and sensitive LC-MS/MS method was established and validated for the determination of 5-hydroxy-4-methoxycanthin-6-one in rat plasma. Small quantities (20 µL) of plasma sample were used for sample preparation. 5-Hydroxy-4-methoxycanthin-6-one and an internal standard (IS, caffeine) were separated using an ACQUITY HSS T3 column (50 × 2.1 mm, 1.7 µm; Waters, Milford, MA, USA). The mobile phase was composed of 0.1% formic acid in water and acetonitrile. Precursor-to-product ion transitions were m/z 267.0 → 168.2 and m/z 195.0 → 138.1 for quantitative monitoring of 5-hydroxy-4-methoxycanthin-6-one and IS, respectively. The assay was linear over the concentration range of 0.5-500 ng/mL (r > 0.99) with the lower limit of quantification 0.5 ng/mL. Other parameters, including intra- and inter-day precision and accuracy, carryover, stability, extraction recovery, matrix effect, and dilution effect, were within acceptable limits. The validated method was successfully applied to pharmacokinetic study in rats after intravenous (5 mg/kg) and oral (10, 25, 50 mg/kg) administration of 5-hydroxy-4-methoxycanthin-6-one. The result indicated that 5-hydroxy-4-methoxycanthin-6-one was quickly absorbed into the blood and reached the highest concentration at ~33.0-42.0 min, with moderate elimination half-life (0.85-2.11 h) and low bioavailability (16.62-24.42%) after oral administration. The study provided valuable information that can be used as a reference for studying other canthinone alkaloids.


Assuntos
Alcaloides/sangue , Alcaloides/farmacocinética , Cromatografia Líquida de Alta Pressão/métodos , Medicamentos de Ervas Chinesas/farmacocinética , Espectrometria de Massas em Tandem/métodos , Alcaloides/química , Animais , Disponibilidade Biológica , Medicamentos de Ervas Chinesas/química , Modelos Lineares , Masculino , Picrasma , Ratos , Ratos Sprague-Dawley , Reprodutibilidade dos Testes , Sensibilidade e Especificidade , Espectrometria de Massas por Ionização por Electrospray/métodos
15.
J Agric Food Chem ; 68(1): 117-127, 2020 Jan 08.
Artigo em Inglês | MEDLINE | ID: mdl-31820963

RESUMO

Six new quassinoids, named kumulactone F (1), kumulactone G (2), kumulactone H (4), kumulactone I (5), kumulactone J (6), and kumulactone K (7), a pair of undescribed epimers α- and ß-nigakihemiacetal G (3), 15 known quassinoids (8-22), and a mixture of the known compounds α- and ß-neoquassin (23) were separated from the dried stems of the medical plants Picrasma quassioides. The chemical structures of all of the new compounds were established by spectroscopic data analyses (HR-ESI-MS, 1D and 2D NMR spectroscopy, and electronic circular dichroism (ECD)). Biologically, compounds 9 and 21 showed toxicity toward the Asian citrus psyllid Diaphorina citri Kuwayama with potent activity even equal to that of the positive control (Abamectin), compound 11 exhibited an excellent neuroprotective effect against SH-SY5Y cells which were pretreated by H2O2 with potent activity equal to that of the positive control (Trolox), and none of them showed cytotoxic activity toward the HeLa or A549 cell lines (IC50 > 100 µM).


Assuntos
Hemípteros/efeitos dos fármacos , Inseticidas/farmacologia , Fármacos Neuroprotetores/farmacologia , Picrasma/química , Extratos Vegetais/farmacologia , Quassinas/farmacologia , Animais , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Hemípteros/crescimento & desenvolvimento , Humanos , Peróxido de Hidrogênio/toxicidade , Inseticidas/química , Neurônios/citologia , Neurônios/efeitos dos fármacos , Fármacos Neuroprotetores/química , Extratos Vegetais/química , Quassinas/química
16.
Nat Prod Res ; 34(4): 489-493, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30369253

RESUMO

(±)-Quassidine K (1), a pair of new bis-ß-carboline alkaloid enantiomers, were isolated from Picrasma quassioides. Their structures were determined on the basis of detailed spectroscopic data analysis. The absolute configurations of (+)-S-quassidine K (1a) and (-)-R-quassidine K (1b) were determined by comparing with the reported experimental ECD spectra after chiral separation. The cytotoxicity assay showed activity against HeLa cells with IC50 values of 15.8 and 20.1 µM, respectively.


Assuntos
Alcaloides/isolamento & purificação , Antineoplásicos/isolamento & purificação , Carbolinas/isolamento & purificação , Picrasma/química , Alcaloides/química , Alcaloides/farmacologia , Antineoplásicos/farmacologia , Carbolinas/química , Carbolinas/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Células HeLa , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Estereoisomerismo
17.
Nat Prod Res ; 34(16): 2289-2294, 2020 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-30600699

RESUMO

Canthin-6-one analogue, 4-methoxy-5-hydroxycanthin-6-one (CAN1) was isolated from Picrasma quassioides (D.Don) Benn., and a series of derivatives containing the CAN1 framework were designed, synthesized, and evaluated for anti-proliferative activity against two human cancer cell lines, HepG2 and HCT116. Among these compounds, the most representative compound d exhibited better anti-proliferative activities in vitro compared with the positive control Fluorouracil (5-FU), with IC50 values of 5.05 µM (HepG2) and 6.65 µM (HCT116), respectively. Compound d triggered more significant HepG2 cell apoptosis than 5-FU did in a dose-dependent manner. Furthermore, western blot assay indicated that d could enhance the expression of p65 while promoting pro-apoptotic proteins and suppressing the anti-apoptotic proteins in a dose-dependent manner. All these results demonstrated that d might be a potential agent for cancer therapy deserving further exploring.


Assuntos
Antineoplásicos/farmacologia , Indóis/farmacologia , Naftiridinas/farmacologia , Picrasma/química , Apoptose/efeitos dos fármacos , Carbolinas , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Desenho de Fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Células Hep G2 , Humanos , Alcaloides Indólicos , Indóis/química , Naftiridinas/química , Relação Estrutura-Atividade , Fator de Transcrição RelA/efeitos dos fármacos
18.
Chin J Nat Med ; 17(12): 906-911, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31882044

RESUMO

A pair of new tirucallane triterpenoid epimers, picraquassins M and N (1> and 2), were isolated from the stems of Picrasma quassioides (D. Don) Benn. Their structures were determined based on comprehensive spectroscopic and X-ray crystallographic analyses. In addition, their AChE inhibitory activity, cytotoxicity against five human tumour cell lines (SW480, MCF-7, HepG2, Hela, and PANC-1), and antimicrobial activity against two bacteria (Staphylococcus. aureus 209P and Escherichia coli ATCC0111) and two fungi (Candida albicans FIM709 and Aspergillus niger R330) were evaluated.


Assuntos
Anti-Infecciosos/química , Picrasma/química , Caules de Planta/química , Triterpenos/química , Anti-Infecciosos/isolamento & purificação , Aspergillus niger/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , Linhagem Celular Tumoral , China , Cristalografia , Escherichia coli/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Staphylococcus aureus/efeitos dos fármacos , Triterpenos/isolamento & purificação
19.
Fitoterapia ; 139: 104375, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31629050

RESUMO

Picrasamide A (1), a new cinnamamide derivative, together with two new ß-carboline alkaloids (2 and 3) and five known ß-carboline alkaloids (4-8) were isolated from the stems of Picrasma quassioides (D. Don) Benn. Their structures were elucidated by detailed analyses of UV, IR, HRESIMS, and NMR data. Compound 1 was the first case of cinnamamide derivative from genus Picrasma. The AChE inhibitory activity and the antimicrobial activity of 1-8 were assessed. In addition, preliminary structure-activity relationships of these ß-carboline alkaloids on the AChE inhibitory activity and antimicrobial activity were proposed.


Assuntos
Antibacterianos/farmacologia , Inibidores da Colinesterase/farmacologia , Cinamatos/farmacologia , Picrasma/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antibacterianos/isolamento & purificação , Carbolinas/isolamento & purificação , Carbolinas/farmacologia , China , Inibidores da Colinesterase/isolamento & purificação , Cinamatos/isolamento & purificação , Testes de Sensibilidade Microbiana , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Caules de Planta/química , Relação Estrutura-Atividade
20.
Bioorg Chem ; 92: 103258, 2019 11.
Artigo em Inglês | MEDLINE | ID: mdl-31520892

RESUMO

Alzheimer disease (AD), a prevalent neurodegenerative disorder, is one of the leading causes of dementia. However, there is no effective drug for this disease to date. Picrasma quassioides (D.Don) Benn, a Chinese traditional medicine, was used mainly for the treatment of inflammation, fever, microbial infection and dysentery. In this paper, we reported that the EtOAc extract of Picrasma quassioides stems showed potential neuroprotective activities in l-glutamate-stimulated PC12 and Aß25-35-stimulated SH-SY5Y cell models, as well as improved memory and cognitive abilities in AD mice induced by amyloid-ß peptide. Moreover, it was revealed that the anti-AD mechanism was related to suppressing neuroinflammatory and reducing Aß1-42 deposition using ELISA assay kits. To clarify the active components of the EtOAc extract of Picrasma quassioides stems, a systematic phytochemistry study led to isolate and identify six ß-carboline alkaloids (1-6), seven canthin-6-one alkaloids (7-13), and five quassinoids (14-18). Among them, four ß-carbolines (1-3, and 6) and six canthin-6-ones (7-11, and 13) exhibited potential neuroprotective activities in vitro. Based on these date, the structure-activity relationships of alkaloids were discussed. Furthermore, molecular docking experiments showed that compounds 2 and 3 have high affinity for both of dual-specificity tyrosine phosphorylation-regulated kinase 1A (DYPKIA) and butyrylcholinesterase (BuChE).


Assuntos
Doença de Alzheimer/tratamento farmacológico , Fármacos Neuroprotetores/farmacologia , Picrasma/química , Extratos Vegetais/farmacologia , Doença de Alzheimer/patologia , Animais , Linhagem Celular Tumoral , Modelos Animais de Doenças , Relação Dose-Resposta a Droga , Humanos , Aprendizagem em Labirinto/efeitos dos fármacos , Camundongos , Camundongos Endogâmicos ICR , Estrutura Molecular , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificação , Células PC12 , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Ratos , Relação Estrutura-Atividade
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